Abstract
A series of parasubstituted tetraphenylporphyrin zirconium(IV) salicylate complexes (SA/5-SSAZr(IV)RTPP, R = p-H, p-CH3, p-NO2, p-Cl, SA = salicylate, and 5-SSA = 5-sulfosalicylate) have been synthesized, and the spectral properties of free base porphyrins, their corresponding metallated, and axially ligated zirconium(IV) porphyrin compounds were compared with each other. A detailed analysis of ultraviolet-visible (UV-vis), proton nulcear magnetic resonance (1H NMR) spectroscopy, infrared (IR) spectroscopy, and elemental analysis suggested the transformation from free base porphyrins to zirconium(IV) porphyrins. The ability of the metal in this complex for extra coordination of solvent molecules was confirmed by ESI-MS spectra. Besides the fluorescence, cyclic voltammetry, and thermogravimetric studies, the complexes were also screened for antimicrobial and anticancer activities. Among all the complexes, 5-SSAZr(p-NO2TPP) shows high antibacterial activity.
Highlights
Synthesis and functionalization of porphyrins [1] have long been of great interest in the chemistry community because of the vast potentials and demands for porphyrin derivatives in diverse fields, such as materials [2, 3], supramolecular chemistry [4, 5], biomimetic models [6], catalysis [7, 8], photodynamic therapy [9], and ionophores [10]
The general synthetic routes to peripherally tetrasubstituted tetraphenylporphyrin derivatives (RTPP), their corresponding metallated, and axially ligated zirconium(IV) porphyrins are shown in Schemes 1, 2, and 3, respectively
We have described the synthesis of pure porphyrins and their subsequent reactions with ZrCl4 and salicylic acid/5-sulfosalicylic acid so as to get their axially ligated Zr(IV) porphyrins
Summary
Synthesis and functionalization of porphyrins [1] have long been of great interest in the chemistry community because of the vast potentials and demands for porphyrin derivatives in diverse fields, such as materials [2, 3], supramolecular chemistry [4, 5], biomimetic models [6], catalysis [7, 8], photodynamic therapy [9], and ionophores [10]. Porphyrins were reported to exhibit a variety of biological activities This is due to the fact that natural and synthetic porphyrins have relatively low toxicity in vitro and in vivo and they possess antitumor [11, 12] and antioxidant effects [13, 14] and have a good potential for metal ions complexation. Bioinorganic Chemistry and Applications a study of axially substituted zirconium(IV) porphyrin with salicylic acid and its derivatives. We believe that these novel compounds will be fundamental substances for potential applications in the future. With this objective, we aimed at the synthesis, spectroscopic characterization, and biological studies on axially substituted zirconium(IV) porphyrins with salicylic acid and 5-sulfosalicylic acid as axial ligands
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